Reaktion #616341

Reaktionsgleichung

tert-butyl (1′-benzyl-1-(5-isopropyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4′-piperidine]-4-yl)methyl(cyclopentyl)carbamate

ammonium formate

→

tert-butyl cyclopentyl((1-(5-isopropyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4′-piperidine]-4-yl)methyl)carbamate

Ausbeute 81.0%

Lösungsmittel

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturheated
2. 2
   Temperaturto reflux for 7 hours
3. 3
   FiltrationThe reaction was filtered through glass
4. 4
   Filtrationfilter paper
5. 5
   Sonstigethe solvent was removed under reduced pressure
6. 6
   SonstigeThe crude residue was purified by column chromatography (5% MeOH/DCM

Vorschrift

A solution of tert-butyl (1′-benzyl-1-(5-isopropyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4′-piperidine]-4-yl)methyl(cyclopentyl)carbamate (0.095 g, 0.15 mmol) in MeOH (1 mL) was treated with Pd/C (0.0079 g, 0.0075 mmol) and ammonium formate (0.028 g, 0.45 mmol) and heated to reflux for 7 hours then stirred at room temperature overnight. The reaction was filtered through glass filter paper, and the solvent was removed under reduced pressure. The crude residue was purified by column chromatography (5% MeOH/DCM then 5% 7N NH4 in MeOH/DCM) to yield tert-butyl cyclopentyl((1-(5-isopropyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4′-piperidine]-4-yl)methyl)carbamate (0.066 g, 81%). LCMS (APCI+) m/z 546.1 [M+H]+; Rt=4.25 min.

Quelle